13159-28-9

Basic information

• Product Name: Betulinicaldehyde
• Synonyms: Betulinicaldehyde;3beta-Hydroxy-Lup-20(30)-en-28-al;Betunal;Lup-20(29)-en-28-al, 3beta-hydroxy-;Nsc 250423;Betulinicaldehyde, 97%, Semi-Synthetic;BETULINIC ALDEHYDE, 98% BY HPLC
• CAS NO: 13159-28-9
• Molecular Formula: C₃₀H₄₈O₂
• Molecular Weight: 440.70092
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 13159-28-9.mol
• Article Data: 28

Chemical Properties

• Melting Point: 183-187 °C(Solv: methanol (67-56-1))
• Boiling Point: 513.909 °C at 760 mmHg
• Flash Point: 217.385 °C
• Appearance: /
• Density: 1.041
• Vapor Pressure: 1.04E-12mmHg at 25°C
• Refractive Index: 1.544
• PKA: 15.17±0.70(Predicted)
• CAS DataBase Reference: Betulinicaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Betulinicaldehyde(13159-28-9)
• EPA Substance Registry System: Betulinicaldehyde(13159-28-9)

Safety Data

• Hazardous Substances Data: 13159-28-9(Hazardous Substances Data)

Usage

General Description

Betulinic aldehyde is a naturally occurring compound found in the bark of the white birch tree and other plants. It is a pentacyclic triterpenoid that has been the subject of extensive research due to its potential pharmaceutical and medicinal properties. Betulinic aldehyde has shown to possess antitumor, anti-inflammatory, antimalarial, and antimicrobial activities. It also exhibits potent inhibitory effects on certain enzymes, making it a potential candidate for drug development. Additionally, betulinic aldehyde has been studied for its potential as an anti-viral and anti-HIV agent. Its diverse and promising biological activities make it an important subject of ongoing investigation in the fields of medicinal chemistry and pharmaceutical science.

InChI:InChI=1/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3

Upstream product

• 473-98-3 betulin 
• 212708-99-1 O,O'-bis-(trimethylsilyl)-betulin 
• 472-15-1 Betulinic acid 
• 10376-50-8 3-O-acetylbetulinic acid 
• 59868-82-5 3-O-acetylbetulinic acid chloride 
• 473-98-3 3β,28-dihydroxy-lup-20(29)-ene 
• 1587722-29-9 3-O-allyl betulinal 
• 1025068-55-6 (3β)-3-acetyloxy-N-methoxy-N-methyl-lup-20(29)-en-28-amide 
• 27570-21-4 3-O-acetylbetulinal 
• 27570-20-3 betulin monoacetate 
• 1721-69-3 betulin diacetate 

Downstream Products

• 1025069-19-5 (3β)-3-[4-(2-phenylmethoxycarbonyl)-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-al 
• 1228273-12-8 (R)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-γ-butyrolactone 
• 473-98-3 betulin 
• 1025068-98-7 4-fluoro-N-[[(3β)-3-hydroxylup-20(29)-en-28-yl]methyl]phenylacetamide 
• 1025069-18-4 (3β)-28-[[(phenylcarbonyl)amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpentanedioate 
• 1025068-79-4 [(3β)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetic acid 
• 1025068-78-3 methyl [(3β)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetate 
• 1025069-17-3 (3β)-28-[[(phenylcarbonyl)amino]methyl]lup-20(29)-en-3-ol; methyl 3,3-dimethylpentanedioate 
• 1025069-72-0 (3β)-28-[[[(2-(4-fluorophenyl)-1-oxo)ethyl]amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpentanedioate 
• 1025070-12-5 [(3β)-N-(2-hydroxy-1,1-dimethylethyl)-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetamide 
• 1025068-99-8 (3β)-28-[[[[2-(4-fluorophenyl)-1-oxo]ethyl]amino]methyl]lup-20(29)-en-3-ol; 2-trimethylsilylethyl 3,3-dimethylpentanedioate 
• 1025069-32-2 [(3β)-N-[3-(4-methyl-1-piperazinyl)propyl]-3-[4-(phenylmethoxy)carbonyl-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-yl]acetamide 
• 545-47-1 lupenol 
• 472-15-1 Betulinic acid 

Relevant articles and documents

POTENTIAL ALLELOPATHIC LUPANE TRITERPENES FROM BIOACTIVE FRACTIONS OF MELILOTUS MESSANENSIS

The aerial parts of Melilotus messanenis (sweet clover) afforded, from the medium polar bioactive fractions, in addition to the known lupane triterpenes lupeol, betulin, betulin aldehyde and betulinic acid, the new norlupane messagenin (30-norlupane-3β,28-diol-20-one) which have been tested as allelochemicals.Structures and their stereochemistries were elucidated by spectral methods and chemical transformations.Messagenin has been synthesized from betulinic acid.The effect of a series of aqueous solutions at 10-4-10-9 M of eight natural and synthetic lupane derivatives were tested for their effects on the germination and growth of the dicotyledon species Lactuca sativa and Lepidium sativum and the monocotyledon species Hordeum vulgare and Triticum aestivum.All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the alleopathic action of Melilotus messanensis. - Key words: Melilotus messanensis; Leguminoseae; Fabaceae; sweet clover; lupane triterpenes; messagenin; 30-nor-lupane-3β,28-diol-20-one; allelopathy; Lactuca sativa; lepidium sativa; Hordeum vulgare; Triticum aestivum.

Preparation of Betulone Via Betulin Oxidation Over Ru Nanoparticles Deposited on Graphitic Carbon Nitride

Derivatives of betulin obtained by oxidation have broad pharmacological applications, demonstrating anti-inflammatory, antioxidant, hepatoprotective, and anticancer activity. Ru supported catalysts based on graphitic carbon nitride or N-doped carbon were prepared via a mild reduction of the initial Ru precursor with hydrazine. These catalysts along with Ru supported on carbon nanofibers and a mesoporous carbon support Sibunit were studied in catalytic oxidation of betulin. Ru/carbon nitride demonstrated catalytic activity in betulin oxidation higher than Ru/N-doped carbon (conversion of betulin up to ca. 70% and 30%, respectively). Selectivity to different oxidation products was dependent on the properties of the carbon supports.

Selective oxidation of betulin by Cr(VI) reagents

Oxidation of betulin by pyridinium dichromate, pyridinium chlorochromate, and K2Cr2O7 - H2SO4 in the presence of tetrabutylammonium bromide was studied. Products of regioselective C-3, C-28-, and exha

Selective oxidation of betulin for the preparation of betulinic acid, an antitumoral compound

This paper describes a semisynthetic approach for the preparation of betulinic acid from betulin. The main step of this synthetic approach is the selective oxidation of primary alcohol function of betulin. This reaction is accomplished with chromic oxide adsorbed on silica gel to obtain betulinal in an adequate yield. Betulinal is then almost quantitatively oxidized to betulinic acid by potassium permanganate action.

Oxidation of a wood extractive betulin to biologically active oxo-derivatives using supported gold catalysts

Betulin (90-94%) was extracted from birch with a non-polar solvent and recrystallized from 2-propanol. Liquid-phase oxidation of betulin aimed at obtaining its biologically active oxo-derivatives (betulone, betulonic and betulinic aldehydes), exhibiting e.g. antitumor, anti-inflammatory, antiparasitic, anticancer and anti-HIV properties, was demonstrated for the first time over gold-based catalysts. Gold was deposited on pristine TiO2 and the same support modified with ceria and lanthana, followed by pretreatment with a H2 or O2 atmosphere. The catalysts were characterized by XRD, BET, ICP, TEM, XPS, DRIFT CO, TPD of NH3 and CO2 methods. The nature of the support, type of modification and the pretreatment atmosphere through the metal-support interactions significantly influenced the average particle size of gold, its distribution and the electronic state of gold, as well as the acid-base properties and, thereby, the catalytic performance (activity and selectivity) in betulin oxidation. Au/La2O3/TiO2 pretreated in H2 displayed the highest catalytic activity in betulin oxidation among the studied catalysts with selectivities to betulone, betulonic and betulinic aldehydes of 42, 32 and 27%, respectively, at 69% conversion. Side reactions resulting in oligomerization/polymerization products occurred on the catalyst surface with the participation of strong acid sites, diminishing the yield of the desired compounds. The latter was improved by adding hydrotalcite with the basic properties to the reaction mixture containing the catalyst. Kinetic modelling through numerical data fitting was performed to quantify the impact of such side reactions and determine the values of rate constants.

Oxidative transformations of betulinol

Starting from commercially available betulinol by a combination of several selective oxidation procedures betutinal, betulinic acid, betulonal as well as betulonic acid were obtained in high yields on a multi-gram scale.

A practical synthesis of betulinic acid

A new synthetic route for the synthesis of betulinic acid from betulin has been developed. The main step of this procedure is the selective oxidation of the primary alcohol function of betulin without affecting the secondary hydroxyl group. Applying shorter reaction times and lower temperatures results in the exclusive formation of the corresponding aldehyde, betulinal.

TRITERPENE AMINE DERIVATIVES

The present invention concerns novel pharmaceutically active triterpene amine derivatives, pharmaceutical compositions containing the same, their use as medicaments, and the use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the triterpene amine compounds. Specifically, the compounds are derivatives of betulinic acid having substitutions at one or more of the C-3, C-28 and C-19 positions as further described herein. The novel compounds are useful as antiretroviral agents. In particular, the novel compounds are useful for the treatment of Human Immunodeficiency Virus-1 (HIV-1).